Windham Mountain Club
The closer option for a straightforward ski day. Check current lift operations, lessons, rentals and mountain conditions before leaving the house.
Visit Windham Mountain Club
Preston Hollow, New York
A Private Catskills Ski Getaway Near Windham
Ski the mountain, then come back to 110 private acres, radiant-heated floors, a gas fireplace and a hot tub under a wide-open Catskill sky.
25 minApprox. to Windham
35 minApprox. to Hunter
5Maximum guests
110 acresNo visible neighbors
The winter experience
Space to warm up—and properly come down
Hollow Sky is close enough for a full ski day and far enough from the resort corridor to feel genuinely private. After the lifts close, the house becomes the destination: soak in the hot tub, sit by the fireplace and let the radiant floors do their work.
The home has two bedrooms, two full baths, a stocked kitchen and room for up to five guests. Large windows keep the landscape present even when the weather says to stay inside.
Choose your mountain
Windham or Hunter
Both mountains work as day trips from Hollow Sky. Drive times are approximate in normal conditions; winter traffic and weather can add time.
Hunter Mountain
A larger alternative with a different trail mix. Confirm operating hours, tickets and the latest conditions on Hunter's official site.
Visit Hunter MountainTwo-night plan
A ski weekend without rushing it
Friday: arrive and settle in
Pick up groceries before the final drive, arrive after 4 p.m., learn the house and keep dinner simple. Finish with the fireplace or hot tub.
Saturday: one full mountain day
Leave with extra winter-driving time, ski Windham or Hunter, then return for dinner at the house and an unhurried evening.
Sunday: slow morning
Make breakfast, walk the property if conditions allow, and use the late morning to enjoy the view before the 11 a.m. checkout.
Adding a third night? Use the extra day for a second mountain, a weather buffer or a completely off-slope day at Hollow Sky. The house is at its best when the schedule has room in it.
Food and provisions
Stock the kitchen, then choose your outing
The most reliable winter plan is to arrive with breakfast and at least one dinner covered. For an outing, these local businesses are useful starting points; check current hours and reservations directly.
Windham
Consider Windham Local for coffee and casual food or Millrock for dinner.
Cairo and Catskill
For the southern approach, look at Red Star Cafe & Bakery, New York Restaurant or Wasana's Thai.
Winter access
Plan for mountain weather
The final approach is a gravel road with an incline, and conditions can change quickly. In snow or ice, an AWD or 4WD vehicle with appropriate tires is strongly recommended. Check the forecast and mountain reports before travel, allow more time than the map suggests and download directions in advance because cell service can be spotty. The house has reliable Starlink Wi-Fi once you arrive.
Safety first: do not treat a storm as part of the adventure. If the forecast is poor, adjust your travel window and contact the host with questions before setting out.
Guest perspective
Comfort after the cold
“So peaceful and relaxing. The pups loved the land. Will definitely book again.”— Keryna, Airbnb guest review
“The amenities were impressive—stunning views and the hot tub, which was the highlight of our stay.”— Sadiyya, Airbnb guest review
Book direct
Make Hollow Sky your winter base
Direct booking is handled securely through Hospitable and the calendar is synchronized across booking channels. Direct reservations avoid platform fees. A separate $500 refundable security deposit applies.
Direct-booking cancellations receive a full refund within 24 hours of booking when check-in is at least seven days away. After that grace period, 50% of the applicable refundable reservation amount is available until 14 days before check-in; reservations are non-refundable inside 14 days.